Synthesis of Heterocyclic Pyridine-Based Chalcones with Dimeric Structure
| dc.citation.epage | 6 | |
| dc.citation.issue | 1 | |
| dc.citation.spage | 1 | |
| dc.contributor.affiliation | Universiti Tunku Abdul Rahman | |
| dc.contributor.author | Lai, Pui-Mun | |
| dc.contributor.author | Ha, Sie-Tiong | |
| dc.coverage.placename | Львів | |
| dc.coverage.placename | Lviv | |
| dc.date.accessioned | 2024-01-22T10:41:25Z | |
| dc.date.available | 2024-01-22T10:41:25Z | |
| dc.date.created | 2022-03-16 | |
| dc.date.issued | 2022-03-16 | |
| dc.description.abstract | Синтезовано три нові гетероциклічні халкони, що містять піридиновий фрагмент. За допомогою ІЧ-спектроскопії, 1Н ЯМР та 13С ЯМР визначено їх хімічну структуру, і встановлено, що вони відносяться до сполук із загальною назвою α,ω-біс{3-(піридин-3-іл)-1-(феніл-4-окси)проп-2-ен-1-он}алкани. Халкони ‒ це димери, що мають симетричну структуру, і відрізняються довжиною алкільного проміжку (CnH2n, де n = 8, 10 або 12). Для визначення фазових переходів синтезованих сполук застосовано метод диференціальної скануючої калориметрії (DSC). Термограми DSC відображають пряму ізотропізацію та перекристалізацію під час процесів нагрівання та охолодження відповідно. Кристалічна фаза перетворюється в ізотропну фазу, не виявляючи жодної мезофази. Вивчено вплив структурно-рідких кристалічних властивостей симетричних димерів, щоб пояснити причини нерідких кристалічних властивостей у діючих халконах. | |
| dc.description.abstract | Three new heterocyclic chalcones containing pyridine moiety were synthesized and their chemical structures were determined via IR, 1H NMR and 13C NMR spectroscopy. General name of these compounds are α,ω-bis{3-(pyridin-3-yl)-1-(phenyl-4-oxy)prop-2-en-1-one}alkanes. The chalcones are dimers having a symmetrical structure and they can be differed by the alkyl spacer length (CnH2n, where n = 8, 10 or 12). Differential scanning calorimetry (DSC) technique was employed to study their phase transition behaviors. DSC thermograms displayed direct isotropization and recrystallization during heating and cooling processes, respectively. The crystal phase turned into isotropic phase without exhibiting any mesophase. Influence of structure-liquid crystalline property relationships of the symmetrical dimers was examined in order to explain the reasons for the non-liquid crystalline properties in the current chalcones. | |
| dc.format.extent | 1-6 | |
| dc.format.pages | 6 | |
| dc.identifier.citation | Lai P. Synthesis of Heterocyclic Pyridine-Based Chalcones with Dimeric Structure / Pui-Mun Lai, Sie-Tiong Ha // Chemistry & Chemical Technology. — Lviv : Lviv Politechnic Publishing House, 2022. — Vol 16. — No 1. — P. 1–6. | |
| dc.identifier.citationen | Lai P. Synthesis of Heterocyclic Pyridine-Based Chalcones with Dimeric Structure / Pui-Mun Lai, Sie-Tiong Ha // Chemistry & Chemical Technology. — Lviv : Lviv Politechnic Publishing House, 2022. — Vol 16. — No 1. — P. 1–6. | |
| dc.identifier.doi | doi.org/10.23939/chcht16.01.001 | |
| dc.identifier.uri | https://ena.lpnu.ua/handle/ntb/60943 | |
| dc.language.iso | en | |
| dc.publisher | Видавництво Львівської політехніки | |
| dc.publisher | Lviv Politechnic Publishing House | |
| dc.relation.ispartof | Chemistry & Chemical Technology, 1 (16), 2022 | |
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| dc.relation.referencesen | [1] Achanta, G.; Modzelewska, A.; Feng, L.; Khan, S.R.; Huang P. A Boronic-Chalcone Derivative Exhibits Potent Anticancer Activity through Inhibition of the Proteasome. Mol. Pharmacol. 2005, 70, 426-433. https://doi.org/10.1124/mol.105.021311 | |
| dc.relation.referencesen | [2] Bukhari, S.N.A.; Jasamai, M.; Jantan, I.; Ahmad, W. Review of Methods and Various Catalysts Used for Chalcone Synthesis. Mini Rev. Org. Chem. 2013, 10, 73-83. https://doi.org/10.2174/1570193X11310010006 | |
| dc.relation.referencesen | [3] Bukhari, S.; Jasamai, M.; Jantan, I. Synthesis and Biological Evaluation of Chalcone Derivatives (Mini Review). Mini Rev. Med. Chem. 2012, 12, 1394-1403. https://doi.org/10.2174/138955712804586648 | |
| dc.relation.referencesen | [4] Saydam, G.; Aydin, H.H.; Şahin, F.; Kucukoglu, O.; Erciyas, E.; Terzioglu, E.; Buyukkeçeci, F.; Omay, S.B. Cytotoxic and Inhibitory Effects of 4,4′-Dihydroxy Chalcone (RVC-588) on Proliferation of Human Leukemic HL-60 Cells. Leukemia Res. 2003, 27, 57-64. https://doi.org/10.1016/S0145-2126(02)00058-9 | |
| dc.relation.referencesen | [5] Mishra, L.; Itokawa, H.; Bastow, K.F.; Tachibana, Y.; Nakanishi, Y.; Kilgore, N.; Lee, K.-H.; Sinha, R. Anti-HIV and Cytotoxic Activities of Ru(II)/Ru(III) Polypyridyl Complexes Containing 2,6-(2′-Benzimidazolyl)-pyridine/chalcone as Co-Ligand. Bioorg. Med. Chem. 2001, 9, 1667-1671. https://doi.org/10.1016/S0968-0896(01)00074-8 | |
| dc.relation.referencesen | [6] Ko, H.-H.; Tsao, L.-T.; Yu, K.-L.; Liu, C.-T.; Wang, J.-P.; Lin, C.-N. Structure-Activity Relationship Studies on Chalcone Derivatives: The Potent Inhibition of Chemical Mediators Release. Bioorg. Med. Chem. 2003, 11, 105-111. https://doi.org/10.1016/S0968-0896(02)00312-7 | |
| dc.relation.referencesen | [7] Tuchinda, P.; Reutrakul, V.; Claeson, P.; Pongprayoon, U.; Sematong, T.; Santisuk, T.; Taylor, W.C. Anti-Inflammatory Cyclohexenyl Chalcone Derivatives in Boesenbergia Pandurate. Phytochem. 2002, 59, 169-173. https://doi.org/10.1016/S0031-9422(01)00451-4 | |
| dc.relation.referencesen | [8] Bukhari, S.N.A.; Jantan, I.B.; Jasamai, M.; Ahmad, W.; Amjad, M.W.B. Synthesis and Biological Evaluation of Curcumin Analogues. Mini Rev. Med. Chem. 2013, 13, 501-513. https://doi.org/10.3923/jms.2013.501.513 | |
| dc.relation.referencesen | [9] Domínguez, J.N.; León, C.; Rodrigues, J.; de Domínguez, N.G.; Gut, J.; Rosenthal, P.J. Synthesis and Evaluation of New Antimalarial Phenylurenyl Chalcone Derivatives. J. Med. Chem. 2005, 48, 3654-3658. https://doi.org/10.1021/jm058208o | |
| dc.relation.referencesen | [10] Shin, D.-M.; Song, D.-M.; Jung, K.-H.; Moon, J.-H. Photochemical Transformation of Chalcone Derivatives. J. Photosci. 2001, 8, 9-12. | |
| dc.relation.referencesen | [11] Suwunwong, T. Syntheses and Fluorescent Properties of Chalcone Derivatives and Heteroarylchalcones. MSc thesis, Prince of Songkla University, Thailand, 2010. | |
| dc.relation.referencesen | [12] Chudgar, N.K.; Shah, S.N. New Fluorescent Mesogens with a Chalcone Central Linkage. Liq. Cryst. 1989, 4, 661-668. https://doi.org/10.1080/02678298908033201 | |
| dc.relation.referencesen | [13] Yeap, G.-Y.; Susanti, I.; Teoh, B.-S.; Mahmood, W.A.K.; Harrison, W.T.A. Synthesis and Phase Transition in New Chalcone Derivatives: Crystal Structure of 1-Phenyl-3-(4′-undecylcarbonyloxyphenyl)-2-propen-1-one. Mol. Cryst. Liq. Cryst. 2005, 442, 133-146. https://doi.org/10.1080/154214090964753 | |
| dc.relation.referencesen | [14] Thaker, B.T.; Patel, P.H.; Vansadiya, A.D.; Kanojiya, J.D. Substitution Effects on the Liquid Crystalline Properties of Thermotropic Liquid Crystals Containing Schiff Base Chalcone Linkages. Mol. Cryst. Liq. Cryst. 2009, 515, 135-147. https://doi.org/10.1080/15421400903291533 | |
| dc.relation.referencesen | [15] Ha, S.T.; Low, Y.W. Synthesis and Phase Transition Behaviours of New Chalcone Derivatives. J. Chem. 2013, 2013. https://doi.org/10.1155/2013/943723 | |
| dc.relation.referencesen | [16] Lim, Y.-W.C.; Ha, S.-T.; Yeap, G.-Y.; Sastry, S.S. Synthesis and Mesomorphic Properties of New Heterocyclic Liquid Crystals with Central Ester-Chalcone Linkages. J. Taibah Univ. Sci. 2017, 11, 133-140. https://doi.org/10.1016/j.jtusci.2015.12.004 | |
| dc.relation.referencesen | [17] Collings, P.J.; Hilger, A. Liquid Crystal: Nature's Delicate Phase of Matter. IOP Publishing Ltd., Bristol, 1990. | |
| dc.relation.referencesen | [18] Yeap, G.-Y.; Al-Taifi, E.A.; Ong, C.-H.; Mahmood, W.A.K.; Takeuchi, D.; Ito, M.M. Synthesis and Phase Transition Studies on Non-Symmetric Liquid Crystal Dimers: N-(4-(n-(4-(Benzothiazol-2-yl)phenoxy)alkyloxy)-benzylidene)-4-chloroanilines. Phase Trans. 2012, 85, 483-496. https://doi.org/10.1080/01411594.2011.624278 | |
| dc.relation.referencesen | [19] Prajapati, A.K.; Bonde, N.L.; Patel, H.N. Mesogenic Schiff's Base Ester with Chloroethyl Tail. Phase Trans. 2005, 78, 507-513. https://doi.org/10.1080/01411590500188876 | |
| dc.relation.referencesen | [20] Parameswara Rao Alapati; Bhuyan, D.; Madhavi Latha, D.; Pardhasaradhi, P.; Pisipati, V.G.K.M.; Datta Prasad, P.V.; Singh, K.N. Study of Molecular Polarizabilities and Orientational Order Parameter in the Nematic Phase of 6.O12O.6 and 7.O12O.7. World J. Condens. Matt. Phys. 2011, 1, 167-174. https://doi.org/10.4236/wjcmp.2011.14025 | |
| dc.relation.referencesen | [21] Gogoi, B.; Alapati, P.R.; Verma, A.L. Phase Transition Studies in Mesogenic Dimers. Cryst. Res. Technol. 2002, 37, 1331-1337. https://doi.org/10.1002/crat.200290010 | |
| dc.relation.referencesen | [22] Yeap, G.-Y.; Hng, T.-C.; Takeuchi, D.; Osakada, K.; Mahmood, W.A.K.; Ito, M.M. Non-Symmetric Liquid Crystal Dimers: High Thermal Stability in Nematic Phase Enhanced by Thiophene-2-Carboxylate Moiety. Mol. Cryst. Liq. Cryst. 2009, 506, 134-149. https://doi.org/10.1080/15421400902987248 | |
| dc.relation.referencesen | [23] Vill, V. Liquid Crystals, Molecular Design of: Calamitics. In Encyclopedia of Materials: Science and Technology; Buschow, K.H.J.; Cahn, R.W.; Flemings, M.C.; Ilschner, B.; Kramer, E.J.; Mahajan, S.; Veyssière, P., Eds.; Elsevier Science Ltd, 2001; pp 4545-4550. https://doi.org/10.1016/B0-08-043152-6/00796-8 | |
| dc.relation.uri | https://doi.org/10.1124/mol.105.021311 | |
| dc.relation.uri | https://doi.org/10.2174/1570193X11310010006 | |
| dc.relation.uri | https://doi.org/10.2174/138955712804586648 | |
| dc.relation.uri | https://doi.org/10.1016/S0145-2126(02)00058-9 | |
| dc.relation.uri | https://doi.org/10.1016/S0968-0896(01)00074-8 | |
| dc.relation.uri | https://doi.org/10.1016/S0968-0896(02)00312-7 | |
| dc.relation.uri | https://doi.org/10.1016/S0031-9422(01)00451-4 | |
| dc.relation.uri | https://doi.org/10.3923/jms.2013.501.513 | |
| dc.relation.uri | https://doi.org/10.1021/jm058208o | |
| dc.relation.uri | https://doi.org/10.1080/02678298908033201 | |
| dc.relation.uri | https://doi.org/10.1080/154214090964753 | |
| dc.relation.uri | https://doi.org/10.1080/15421400903291533 | |
| dc.relation.uri | https://doi.org/10.1155/2013/943723 | |
| dc.relation.uri | https://doi.org/10.1016/j.jtusci.2015.12.004 | |
| dc.relation.uri | https://doi.org/10.1080/01411594.2011.624278 | |
| dc.relation.uri | https://doi.org/10.1080/01411590500188876 | |
| dc.relation.uri | https://doi.org/10.4236/wjcmp.2011.14025 | |
| dc.relation.uri | https://doi.org/10.1002/crat.200290010 | |
| dc.relation.uri | https://doi.org/10.1080/15421400902987248 | |
| dc.relation.uri | https://doi.org/10.1016/B0-08-043152-6/00796-8 | |
| dc.rights.holder | © Національний університет “Львівська політехніка”, 2022 | |
| dc.rights.holder | © Lai P.-M., Ha S.-T., 2022 | |
| dc.subject | гетероцикл | |
| dc.subject | піридин | |
| dc.subject | халкон | |
| dc.subject | димер | |
| dc.subject | синтез | |
| dc.subject | heterocycle | |
| dc.subject | pyridine | |
| dc.subject | chalcone | |
| dc.subject | dimer | |
| dc.subject | synthesis | |
| dc.title | Synthesis of Heterocyclic Pyridine-Based Chalcones with Dimeric Structure | |
| dc.title.alternative | Синтез гетероциклічних халконів димерної структури на основі піридину | |
| dc.type | Article |
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